# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Ivana Radosavljevic Evans' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'John Evans' ; ? # Address 2 ; ; ? # Footnote 2 ; 'J Howard' '' '' 'Mark R Johnson' '' '' 'Stella R Postlethwaite' '' '' _publ_contact_author_name 'Ivana Radosavljevic Evans' _publ_contact_author_email IVANA.RADOSAVLJEVIC@DURHAM.AC.UK _publ_section_title ; Polymorphism and Hydrogen Bonding in Chincomeronic Acid: a Variable Temperature Experimental and Computational Study ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_requested_journal 'Section E' # Attachment '34pdca_II_120K.cif' data_CRYSTALS_cifI _database_code_depnum_ccdc_archive 'CCDC 686367' _audit_creation_date 07-01-22 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.5942(14) _cell_length_b 7.3317(13) _cell_length_c 12.113(2) _cell_angle_alpha 90 _cell_angle_beta 104.339(4) _cell_angle_gamma 90 _cell_volume 653.4(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '? ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C7 H5 N1 O4 # Dc = 1.70 Fooo = 344.00 Mu = 1.43 M = 167.12 # Found Formula = C7 H5 N1 O4 # Dc = 1.70 FOOO = 344.00 Mu = 1.43 M = 167.12 _chemical_formula_sum 'C7 H5 N1 O4' _chemical_formula_moiety 'C7 H5 N1 O4' _chemical_compound_source ? _chemical_formula_weight 167.12 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.12 _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.143 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 4209 _reflns_number_total 1707 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 1707 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1840 _diffrn_reflns_theta_min 2.768 _diffrn_reflns_theta_max 29.614 _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 27.837 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.80 _refine_diff_density_max 0.95 _refine_ls_number_reflns 1250 _refine_ls_number_restraints 1 _refine_ls_number_parameters 130 #_refine_ls_R_factor_ref 0.0792 _refine_ls_wR_factor_ref 0.1504 _refine_ls_goodness_of_fit_ref 0.8061 #_reflns_number_all 1701 _refine_ls_R_factor_all 0.1027 _refine_ls_wR_factor_all 0.1568 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1250 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_gt 0.1504 _refine_ls_shift/su_max 0.000649 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 19.0 25.1 8.01 ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.7075(4) -0.0868(4) 0.6903(2) 0.0196 1.0000 Uani . . . . . . O1 O 0.7399(4) -0.5926(3) 0.5356(2) 0.0270 1.0000 Uani . . . . . . O4 O 0.7220(4) -0.5978(3) 0.9527(2) 0.0238 1.0000 Uani . . . . . . C5 C 0.7847(4) -0.0813(4) 0.8034(3) 0.0163 1.0000 Uani D . . . . . O2 O 0.6116(5) -0.7172(4) 0.6647(3) 0.0395 1.0000 Uani . . . . . . C3 C 0.7829(4) -0.4063(4) 0.8105(2) 0.0128 1.0000 Uani . . . . . . C2 C 0.7141(4) -0.4100(4) 0.6910(2) 0.0128 1.0000 Uani . . . . . . C1 C 0.6757(4) -0.2466(4) 0.6327(3) 0.0153 1.0000 Uani . . . . . . C4 C 0.8219(4) -0.2387(4) 0.8653(3) 0.0166 1.0000 Uani . . . . . . O3 O 0.9347(4) -0.6868(4) 0.8650(3) 0.0434 1.0000 Uani . . . . . . C7 C 0.8185(4) -0.5810(4) 0.8789(2) 0.0153 1.0000 Uani . . . . . . C6 C 0.6813(4) -0.5893(4) 0.6264(2) 0.0153 1.0000 Uani . . . . . . H2 H 0.875(5) -0.233(5) 0.946(3) 0.017(9) 1.0000 Uiso . . . . . . H1 H 0.627(5) -0.243(5) 0.549(3) 0.015(9) 1.0000 Uiso . . . . . . H3 H 0.822(6) 0.031(4) 0.838(3) 0.035(12) 1.0000 Uiso D . . . . . H5 H 0.669(6) 0.040(7) 0.648(4) 0.037(12) 1.0000 Uiso . . . . . . H4 H 0.731(10) -0.750(10) 0.992(6) 0.10(3) 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0211(12) 0.0150(13) 0.0243(14) 0.0051(11) 0.0088(10) 0.0039(10) O1 0.0474(15) 0.0160(11) 0.0233(12) -0.0049(10) 0.0198(11) -0.0042(11) O4 0.0367(13) 0.0155(11) 0.0240(12) 0.0043(10) 0.0167(10) 0.0020(10) C5 0.0190(13) 0.0087(13) 0.0225(15) -0.0057(12) 0.0077(11) -0.0041(11) O2 0.0589(19) 0.0248(13) 0.0478(16) -0.0193(13) 0.0376(15) -0.0238(14) C3 0.0119(11) 0.0113(13) 0.0162(13) 0.0018(11) 0.0052(10) 0.0007(10) C2 0.0091(11) 0.0130(13) 0.0170(14) -0.0011(11) 0.0042(9) -0.0001(10) C1 0.0163(13) 0.0142(14) 0.0162(13) 0.0020(11) 0.0058(10) 0.0005(11) C4 0.0160(13) 0.0183(15) 0.0159(13) -0.0043(12) 0.0049(10) -0.0033(11) O3 0.0485(17) 0.0348(16) 0.0591(19) 0.0304(15) 0.0366(15) 0.0281(14) C7 0.0150(12) 0.0140(14) 0.0155(13) 0.0056(11) 0.0013(10) 0.0032(11) C6 0.0145(12) 0.0149(13) 0.0155(13) -0.0040(12) 0.0018(10) -0.0014(11) _refine_ls_extinction_coef 56(4) _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C5 . 1.350(4) yes N1 . C1 . 1.354(4) yes N1 . H5 . 1.07(5) no O1 . H4 4_534 1.27(7) no O1 . C6 . 1.284(4) yes O4 . C7 . 1.294(4) yes O4 . H4 . 1.21(7) no C5 . C4 . 1.368(4) yes C5 . H3 . 0.935(18) no O2 . C6 . 1.224(4) yes C3 . C2 . 1.412(4) yes C3 . C4 . 1.393(4) yes C3 . C7 . 1.513(4) yes C2 . C1 . 1.385(4) yes C2 . C6 . 1.518(4) yes C1 . H1 . 0.99(4) no C4 . H2 . 0.96(4) no O3 . C7 . 1.218(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 . N1 . C1 . 121.7(3) yes C5 . N1 . H5 . 117(3) no C1 . N1 . H5 . 121(2) no H4 4_534 O1 . C6 . 112(3) no C7 . O4 . H4 . 112(3) no N1 . C5 . C4 . 120.7(3) yes N1 . C5 . H3 . 119(3) no C4 . C5 . H3 . 120(3) no C2 . C3 . C4 . 119.2(3) yes C2 . C3 . C7 . 121.1(3) yes C4 . C3 . C7 . 119.8(2) yes C3 . C2 . C1 . 118.9(3) yes C3 . C2 . C6 . 121.1(3) yes C1 . C2 . C6 . 120.0(3) yes C2 . C1 . N1 . 119.9(3) yes C2 . C1 . H1 . 122(2) no N1 . C1 . H1 . 119(2) no C3 . C4 . C5 . 119.5(3) yes C3 . C4 . H2 . 120(2) no C5 . C4 . H2 . 120(2) no C3 . C7 . O4 . 113.9(3) yes C3 . C7 . O3 . 120.0(3) yes O4 . C7 . O3 . 126.0(3) yes C2 . C6 . O1 . 114.3(3) yes C2 . C6 . O2 . 119.9(3) yes O1 . C6 . O2 . 125.7(3) yes O4 . H4 . O1 4_535 179(6) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H5 . O2 1_565 146 1.07 1.85 2.803(2) yes O4 . H4 . O1 4_535 179 1.21 1.27 2.471(2) yes # Attachment '34pdca_II_400K.cif' data_CRYSTALS_cifII _database_code_depnum_ccdc_archive 'CCDC 686368' _audit_creation_date 07-01-17 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '400Kbeta in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.7185(14) _cell_length_b 7.3248(13) _cell_length_c 12.179(2) _cell_angle_alpha 90 _cell_angle_beta 103.884(4) _cell_angle_gamma 90 _cell_volume 668.4(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C7 H5 N1 O4 # Dc = 1.66 Fooo = 344.00 Mu = 1.40 M = 167.12 # Found Formula = C7 H5 N1 O4 # Dc = 1.66 FOOO = 344.00 Mu = 1.40 M = 167.12 _chemical_formula_sum 'C7 H5 N1 O4' _chemical_formula_moiety 'C7 H5 N1 O4' _chemical_compound_source ? _chemical_formula_weight 167.12 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.140 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 4293 _reflns_number_total 1738 _diffrn_reflns_av_R_equivalents 0.048 # Number of reflections with Friedels Law is 1738 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1850 _diffrn_reflns_theta_min 2.718 _diffrn_reflns_theta_max 29.772 _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 27.986 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.58 _refine_ls_number_reflns 998 _refine_ls_number_restraints 0 _refine_ls_number_parameters 130 #_refine_ls_R_factor_ref 0.0792 _refine_ls_wR_factor_ref 0.1261 _refine_ls_goodness_of_fit_ref 0.7352 #_reflns_number_all 1732 _refine_ls_R_factor_all 0.1311 _refine_ls_wR_factor_all 0.1353 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 998 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_gt 0.1261 _refine_ls_shift/su_max 0.000103 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 16.5 21.9 7.11 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.7083(5) -0.0894(5) 0.6919(3) 0.0458 1.0000 Uani . . . . . . O1 O 0.7420(5) -0.5938(4) 0.5388(3) 0.0619 1.0000 Uani . . . . . . O4 O 0.7216(5) -0.5991(4) 0.9503(3) 0.0538 1.0000 Uani . . . . . . C5 C 0.7828(6) -0.0848(5) 0.8030(4) 0.0360 1.0000 Uani . . . . . . O2 O 0.6129(6) -0.7171(4) 0.6642(3) 0.0724 1.0000 Uani . . . . . . C3 C 0.7802(4) -0.4085(5) 0.8093(3) 0.0268 1.0000 Uani . . . . . . C2 C 0.7150(4) -0.4124(5) 0.6919(3) 0.0275 1.0000 Uani . . . . . . C1 C 0.6773(5) -0.2488(5) 0.6342(3) 0.0338 1.0000 Uani . . . . . . C4 C 0.8194(5) -0.2399(5) 0.8631(4) 0.0370 1.0000 Uani . . . . . . O3 O 0.9296(5) -0.6870(5) 0.8645(3) 0.0774 1.0000 Uani . . . . . . C7 C 0.8178(5) -0.5816(5) 0.8786(3) 0.0341 1.0000 Uani . . . . . . C6 C 0.6841(5) -0.5914(5) 0.6276(3) 0.0327 1.0000 Uani . . . . . . H1 H 0.631(5) -0.246(6) 0.553(3) 0.042(11) 1.0000 Uiso . . . . . . H2 H 0.869(6) -0.232(6) 0.939(4) 0.052(13) 1.0000 Uiso . . . . . . H3 H 0.818(6) 0.012(6) 0.831(4) 0.046(12) 1.0000 Uiso . . . . . . H5 H 0.678(7) 0.033(8) 0.649(5) 0.078(16) 1.0000 Uiso . . . . . . H4 H 0.729(9) -0.744(11) 0.993(5) 0.13(3) 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.059(2) 0.0242(17) 0.059(3) 0.010(2) 0.0230(19) 0.0064(17) O1 0.115(3) 0.0337(15) 0.0495(19) -0.0125(14) 0.045(2) -0.0108(17) O4 0.084(2) 0.0343(15) 0.054(2) 0.0155(14) 0.0374(17) 0.0078(15) C5 0.050(2) 0.0151(17) 0.043(2) -0.0067(19) 0.0122(17) -0.0048(16) O2 0.113(3) 0.0365(16) 0.087(3) -0.0255(17) 0.062(2) -0.0358(19) C3 0.0295(18) 0.0192(15) 0.033(2) -0.0005(17) 0.0099(14) -0.0002(14) C2 0.0299(18) 0.0243(16) 0.029(2) -0.0034(18) 0.0091(14) -0.0021(15) C1 0.043(2) 0.0252(17) 0.0342(18) 0.0026(15) 0.0123(17) 0.0026(15) C4 0.044(2) 0.0335(19) 0.0330(18) -0.0086(17) 0.0081(17) -0.0036(16) O3 0.088(3) 0.060(2) 0.101(3) 0.046(2) 0.056(2) 0.043(2) C7 0.042(2) 0.0271(17) 0.0335(19) 0.0030(17) 0.0090(16) 0.0029(16) C6 0.0381(19) 0.0245(16) 0.0337(19) -0.0068(16) 0.0049(16) -0.0012(16) _refine_ls_extinction_coef 54(4) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.539(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C5 . 1.337(5) yes N1 . C1 . 1.354(5) yes N1 . H5 . 1.04(6) no O1 . H4 4_534 1.30(8) no O1 . C6 . 1.265(4) yes O4 . C7 . 1.281(4) yes O4 . H4 . 1.18(8) no C5 . C4 . 1.345(5) yes C5 . H3 . 0.81(5) no O2 . C6 . 1.211(4) yes C3 . C2 . 1.399(4) yes C3 . C4 . 1.397(5) yes C3 . C7 . 1.512(5) yes C2 . C1 . 1.384(5) yes C2 . C6 . 1.516(5) yes C1 . H1 . 0.97(4) no C4 . H2 . 0.92(4) no O3 . C7 . 1.201(5) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 . N1 . C1 . 121.8(4) yes C5 . N1 . H5 . 119(3) no C1 . N1 . H5 . 120(3) no H4 4_534 O1 . C6 . 112(3) no C7 . O4 . H4 . 115(3) no N1 . C5 . C4 . 120.9(4) yes N1 . C5 . H3 . 118(3) no C4 . C5 . H3 . 120(3) no C2 . C3 . C4 . 118.8(4) yes C2 . C3 . C7 . 121.9(3) yes C4 . C3 . C7 . 119.3(3) yes C3 . C2 . C1 . 118.8(4) yes C3 . C2 . C6 . 121.3(3) yes C1 . C2 . C6 . 119.9(3) yes C2 . C1 . N1 . 119.6(4) yes C2 . C1 . H1 . 121(2) no N1 . C1 . H1 . 119(2) no C3 . C4 . C5 . 119.9(4) yes C3 . C4 . H2 . 121(3) no C5 . C4 . H2 . 119(3) no C3 . C7 . O4 . 113.5(3) yes C3 . C7 . O3 . 120.5(3) yes O4 . C7 . O3 . 126.0(4) yes C2 . C6 . O1 . 114.1(3) yes C2 . C6 . O2 . 119.7(3) yes O1 . C6 . O2 . 126.1(3) yes O4 . H4 . O1 4_535 177(6) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H5 . O2 1_565 144 1.04 1.92 2.824(2) yes O4 . H4 . O1 4_535 177 1.18 1.30 2.483(2) yes # Attachment '34pdca_I_120K.cif' data_CRYSTALS_cifIII _database_code_depnum_ccdc_archive 'CCDC 686369' _audit_creation_date 07-11-09 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '120sad in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.2948(5) _cell_length_b 11.1107(11) _cell_length_c 11.1385(11) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 655.27(11) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C30 H22 N4 O8 # Dc = 1.44 Fooo = 344.00 Mu = 1.06 M = 141.63 # Found Formula = C28 H20 N4 O16 # Dc = 1.69 FOOO = 344.00 Mu = 1.42 M = 167.12 _chemical_formula_sum 'C28 H20 N4 O16' _chemical_formula_moiety 'C28 H20 N4 O16' _chemical_compound_source ? _chemical_formula_weight 668.48 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.142 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details 'DIFABS (Walker & Stuart, 1983)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 5188 _reflns_number_total 1887 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections with Friedels Law is 1118 # Number of reflections without Friedels Law is 1887 # Theoretical number of reflections is about 955 _diffrn_reflns_theta_min 3.658 _diffrn_reflns_theta_max 29.993 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.094 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.16 _refine_diff_density_max 0.29 _refine_ls_number_reflns 1709 _refine_ls_number_restraints 0 _refine_ls_number_parameters 130 #_refine_ls_R_factor_ref 0.0303 _refine_ls_wR_factor_ref 0.0663 _refine_ls_goodness_of_fit_ref 0.8822 #_reflns_number_all 1885 _refine_ls_R_factor_all 0.0337 _refine_ls_wR_factor_all 0.0670 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1709 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_gt 0.0663 _refine_ls_shift/su_max 0.000246 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.77 3.53 1.16 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Walker, N., & Stuart, (1983). D. Acta Cryst, A39, 158-166. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.03487(19) 0.15715(9) 0.64334(9) 0.0169 1.0000 Uani . . . . . . N1 N 0.6740(2) 0.05308(11) 0.44822(10) 0.0167 1.0000 Uani . . . . . . O4 O 0.5123(2) -0.18618(9) 0.81794(9) 0.0200 1.0000 Uani . . . . . . O2 O 0.2238(2) 0.07111(10) 0.80207(9) 0.0206 1.0000 Uani . . . . . . C2 C 0.3869(2) 0.03108(12) 0.60893(11) 0.0125 1.0000 Uani . . . . . . C7 C 0.3797(2) -0.16468(11) 0.72820(11) 0.0134 1.0000 Uani . . . . . . O3 O 0.1651(2) -0.20689(10) 0.70553(10) 0.0232 1.0000 Uani . . . . . . C6 C 0.2037(2) 0.08845(11) 0.69489(12) 0.0135 1.0000 Uani . . . . . . C3 C 0.4854(2) -0.08381(11) 0.63078(11) 0.0124 1.0000 Uani . . . . . . C5 C 0.7736(3) -0.05590(13) 0.46798(12) 0.0173 1.0000 Uani . . . . . . C4 C 0.6805(2) -0.12770(13) 0.55876(12) 0.0165 1.0000 Uani . . . . . . C1 C 0.4831(3) 0.09764(11) 0.51433(11) 0.0157 1.0000 Uani . . . . . . H1 H 0.426(4) 0.1782(17) 0.4967(16) 0.016(4) 1.0000 Uiso . . . . . . H2 H 0.749(4) -0.2075(17) 0.5665(16) 0.021(5) 1.0000 Uiso . . . . . . H3 H 0.910(3) -0.0765(16) 0.4188(16) 0.015(4) 1.0000 Uiso . . . . . . H5 H 0.749(4) 0.0974(18) 0.3921(18) 0.023(5) 1.0000 Uiso . . . . . . H4 H -0.027(6) 0.207(2) 0.700(2) 0.059(8) 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0162(4) 0.0180(4) 0.0164(4) -0.0018(4) -0.0014(3) 0.0043(4) N1 0.0170(5) 0.0189(6) 0.0143(5) -0.0016(4) 0.0029(4) -0.0061(4) O4 0.0193(5) 0.0209(5) 0.0198(4) 0.0055(4) -0.0044(4) -0.0009(4) O2 0.0234(5) 0.0232(5) 0.0152(5) 0.0031(4) 0.0035(4) 0.0079(4) C2 0.0111(5) 0.0135(6) 0.0128(5) -0.0008(4) 0.0007(4) -0.0011(4) C7 0.0156(5) 0.0109(5) 0.0139(5) -0.0004(4) 0.0011(4) 0.0003(4) O3 0.0199(5) 0.0274(5) 0.0222(5) 0.0083(4) -0.0062(4) -0.0105(4) C6 0.0128(5) 0.0121(5) 0.0156(6) 0.0004(4) 0.0024(4) 0.0004(4) C3 0.0114(5) 0.0132(5) 0.0127(5) 0.0000(4) -0.0017(4) -0.0018(4) C5 0.0131(5) 0.0222(6) 0.0165(6) -0.0043(5) 0.0030(4) -0.0024(5) C4 0.0131(5) 0.0179(6) 0.0184(6) -0.0030(5) 0.0002(4) 0.0015(4) C1 0.0179(6) 0.0140(6) 0.0153(5) -0.0002(4) 0.0009(5) -0.0020(5) _refine_ls_extinction_coef 5(4) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.4031(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C6 . 1.3084(15) yes O1 . H4 . 0.90(3) no N1 . C5 . 1.3388(18) yes N1 . C1 . 1.3452(17) yes N1 . H5 . 0.89(2) no O4 . C7 . 1.2445(16) yes O2 . C6 . 1.2140(16) yes C2 . C6 . 1.5045(18) yes C2 . C3 . 1.4002(18) yes C2 . C1 . 1.3844(17) yes C7 . O3 . 1.2552(16) yes C7 . C3 . 1.5157(17) yes C3 . C4 . 1.3961(18) yes C5 . C4 . 1.3790(19) yes C5 . H3 . 0.935(18) no C4 . H2 . 0.961(19) no C1 . H1 . 0.965(19) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 . O1 . H4 . 107.5(19) no C5 . N1 . C1 . 122.60(12) yes C5 . N1 . H5 . 116.2(13) no C1 . N1 . H5 . 121.0(13) no C6 . C2 . C3 . 121.04(11) yes C6 . C2 . C1 . 119.68(12) yes C3 . C2 . C1 . 118.84(12) yes O4 . C7 . O3 . 126.90(13) yes O4 . C7 . C3 . 118.73(12) yes O3 . C7 . C3 . 114.31(11) yes C2 . C6 . O1 . 114.10(11) yes C2 . C6 . O2 . 120.15(12) yes O1 . C6 . O2 . 125.73(12) yes C7 . C3 . C2 . 121.83(11) yes C7 . C3 . C4 . 118.52(11) yes C2 . C3 . C4 . 119.61(12) yes N1 . C5 . C4 . 120.21(13) yes N1 . C5 . H3 . 115.4(11) no C4 . C5 . H3 . 124.4(11) no C3 . C4 . C5 . 118.93(12) yes C3 . C4 . H2 . 123.2(12) no C5 . C4 . H2 . 117.8(12) no C2 . C1 . N1 . 119.77(12) yes C2 . C1 . H1 . 122.3(11) no N1 . C1 . H1 . 117.8(11) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H5 . O4 4_654 160 0.89 1.80 2.655(2) yes O1 . H4 . O3 3_556 174 0.90 1.60 2.497(2) yes # Attachment '34pdca_I_400K.cif' data_CRYSTALS_cifIV _database_code_depnum_ccdc_archive 'CCDC 686370' _audit_creation_date 07-11-09 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '400sad in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.260(2) _cell_length_b 11.201(5) _cell_length_c 11.275(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 664.3(5) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C30 H22 N4 O8 # Dc = 1.42 Fooo = 344.00 Mu = 1.05 M = 141.63 # Found Formula = C28 H20 N4 O16 # Dc = 1.67 FOOO = 344.00 Mu = 1.40 M = 167.12 _chemical_formula_sum 'C28 H20 N4 O16' _chemical_formula_moiety 'C28 H20 N4 O16' _chemical_compound_source ? _chemical_formula_weight 668.48 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.140 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_T_max 1.0000 _diffrn_measurement_device_type Unknown _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 293 _diffrn_reflns_number 5249 _reflns_number_total 1907 _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections with Friedels Law is 1130 # Number of reflections without Friedels Law is 1907 # Theoretical number of reflections is about 965 _diffrn_reflns_theta_min 3.614 _diffrn_reflns_theta_max 29.986 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.788 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.19 _refine_ls_number_reflns 1390 _refine_ls_number_restraints 0 _refine_ls_number_parameters 130 #_refine_ls_R_factor_ref 0.0323 _refine_ls_wR_factor_ref 0.0643 _refine_ls_goodness_of_fit_ref 0.8776 #_reflns_number_all 1903 _refine_ls_R_factor_all 0.0423 _refine_ls_wR_factor_all 0.0660 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1390 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_gt 0.0643 _refine_ls_shift/su_max 0.000251 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.33 2.93 0.930 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.2925(3) 0.39568(12) 0.40997(14) 0.0441 1.0000 Uani . . . . . . O4 O 0.7521(3) 0.57122(13) 0.07222(13) 0.0486 1.0000 Uani . . . . . . O2 O 0.4757(3) 0.55348(13) 0.32612(15) 0.0561 1.0000 Uani . . . . . . C2 C 0.6396(3) 0.36293(15) 0.28329(15) 0.0292 1.0000 Uani . . . . . . N1 N 0.9249(3) 0.20344(14) 0.30200(16) 0.0409 1.0000 Uani . . . . . . C3 C 0.7318(3) 0.38397(13) 0.16945(15) 0.0282 1.0000 Uani . . . . . . C7 C 0.6242(4) 0.48102(15) 0.09004(15) 0.0316 1.0000 Uani . . . . . . O3 O 0.4175(3) 0.45603(15) 0.04509(16) 0.0603 1.0000 Uani . . . . . . C6 C 0.4573(3) 0.44741(16) 0.34159(15) 0.0332 1.0000 Uani . . . . . . C1 C 0.7388(4) 0.26957(16) 0.34751(17) 0.0375 1.0000 Uani . . . . . . C4 C 0.9231(4) 0.31165(19) 0.12479(19) 0.0402 1.0000 Uani . . . . . . C5 C 1.0181(4) 0.22253(18) 0.1936(2) 0.0431 1.0000 Uani . . . . . . H1 H 0.664(4) 0.2500(19) 0.4254(18) 0.037(5) 1.0000 Uiso . . . . . . H3 H 1.147(4) 0.174(2) 0.170(2) 0.047(6) 1.0000 Uiso . . . . . . H2 H 0.993(5) 0.324(2) 0.046(2) 0.047(6) 1.0000 Uiso . . . . . . H5 H 1.012(5) 0.145(3) 0.350(3) 0.073(8) 1.0000 Uiso . . . . . . H4 H 0.213(7) 0.453(3) 0.461(3) 0.085(10) 1.0000 Uiso . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0446(8) 0.0391(7) 0.0486(8) -0.0041(6) 0.0162(7) -0.0024(6) O4 0.0555(9) 0.0438(7) 0.0466(8) 0.0115(6) -0.0087(7) -0.0150(7) O2 0.0690(10) 0.0331(8) 0.0663(10) 0.0115(7) 0.0287(8) 0.0130(7) C2 0.0301(8) 0.0283(8) 0.0292(9) -0.0005(6) -0.0024(7) 0.0015(6) N1 0.0435(10) 0.0319(8) 0.0473(10) -0.0021(7) -0.0145(8) 0.0088(7) C3 0.0278(8) 0.0281(7) 0.0287(8) 0.0009(6) -0.0040(7) -0.0020(6) C7 0.0362(9) 0.0330(9) 0.0256(8) 0.0017(7) -0.0006(7) 0.0001(7) O3 0.0529(9) 0.0531(9) 0.0750(11) 0.0251(8) -0.0330(9) -0.0170(8) C6 0.0365(9) 0.0346(9) 0.0285(8) 0.0013(7) 0.0009(7) 0.0066(8) C1 0.0475(10) 0.0323(8) 0.0327(9) 0.0021(7) -0.0030(9) 0.0025(8) C4 0.0374(10) 0.0449(11) 0.0383(10) -0.0045(8) 0.0079(8) 0.0035(8) C5 0.0366(10) 0.0389(10) 0.0539(12) -0.0097(9) -0.0025(9) 0.0116(8) _refine_ls_extinction_coef 12(5) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.4083(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C6 . 1.297(2) yes O1 . H4 . 0.95(3) no O4 . C7 . 1.230(2) yes O2 . C6 . 1.205(2) yes C2 . C3 . 1.392(2) yes C2 . C6 . 1.499(2) yes C2 . C1 . 1.375(2) yes N1 . C1 . 1.330(3) yes N1 . C5 . 1.334(3) yes N1 . H5 . 0.97(3) no C3 . C7 . 1.518(2) yes C3 . C4 . 1.387(3) yes C7 . O3 . 1.232(2) yes C1 . H1 . 0.99(2) no C4 . C5 . 1.360(3) yes C4 . H2 . 0.97(2) no C5 . H3 . 0.91(2) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 . O1 . H4 . 110.6(19) no C3 . C2 . C6 . 121.36(15) yes C3 . C2 . C1 . 118.81(16) yes C6 . C2 . C1 . 119.47(16) yes C1 . N1 . C5 . 122.32(18) yes C1 . N1 . H5 . 120.8(17) no C5 . N1 . H5 . 116.5(17) no C2 . C3 . C7 . 122.35(15) yes C2 . C3 . C4 . 119.27(17) yes C7 . C3 . C4 . 118.35(16) yes C3 . C7 . O4 . 118.72(16) yes C3 . C7 . O3 . 114.15(16) yes O4 . C7 . O3 . 127.02(18) yes C2 . C6 . O1 . 113.97(16) yes C2 . C6 . O2 . 120.53(17) yes O1 . C6 . O2 . 125.47(17) yes C2 . C1 . N1 . 119.98(18) yes C2 . C1 . H1 . 119.1(13) no N1 . C1 . H1 . 120.8(13) no C3 . C4 . C5 . 119.23(18) yes C3 . C4 . H2 . 121.8(14) no C5 . C4 . H2 . 118.9(14) no C4 . C5 . N1 . 120.36(19) yes C4 . C5 . H3 . 123.4(15) no N1 . C5 . H3 . 116.2(15) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H5 . O4 3_745 162 0.97 1.73 2.663(2) yes O1 . H4 . O3 4_565 179 0.95 1.56 2.510(2) yes